Expeditious Construction of Spiro-Pyrrolidines by an Autocatalytic One-Pot, Five-Component, 1,3-Dipolar Cycloaddition of in situ Generated Azomethine Ylides and Olefinic Dipolarophiles

Two series of previously unknown spiro-pyrrolidine derivatives were prepared by a five-component reaction that employed ninhydrin, 1,2-phenylenediamine, sarcosine, aldehydes, and malononitrile or cyanoacetic ester in a solvothermal synthesis. This is the first report of an autocatalytic five-component reaction involving a classical Huisgen reaction, in which the dipole - an azomethine ylide - and the dipolarophile were simultaneously generated in situ. The 1,3-dipolar cycloaddition reaction was found to proceed in a highly regio- and diastereoselective manner. The methodology for the preparation of the spiro-pyrrolidines could be an ideal tool for green chemistry and the synthesis of alkaloids.